Description
3-Maleimidopropionic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.
Chemical Properties
White to Pale Yellow Solid
Uses
3-Maleimidopropionic acid is a sulfhydryl reactive heterobifunctional crosslinking reagent.
Application
3-Maleimidopropionic acid (3MP) is a molecule that can be used for the treatment of cancer. 3MP has been shown to inhibit the growth of tumor cells and induce apoptosis. It also inhibits the production of reactive oxygen species, which are produced by cancer cells as a result of chemotherapy. 3MP has potent inhibitory activity against bacterial organisms such as methicillin-resistant Staphylococcus aureus (MRSA) and Clostridium perfringens and antiviral properties against HIV infection. This molecule can also be used in conjunction with monoclonal antibodies or other immunotherapy techniques to improve their efficacy.
General Description
N-Maleoyl-β-alanine (3-maleimidopropanoic acid) is an aliphatic
N-substituted maleimide. It is one of the component of the stabilizing solution for EC145 (a folate-targeted vinca alkaloid conjugate) used in rodent pharmacokinetic studies.
Synthesis
An acetic acid solution of maleic anhydride (5.00 g in 50 mL) was added dropwise to an acetic acid solution of β-alanine (4.54 g in 50 mL). The mixture was stirred at room temperature. After 3 h, AcOH (70 mL ) was added and the temperature was raised to 115 °C under stirred overnight. After 1 hour, an orange oil was obtained. The solvent excess was removed under reduced pressure and the product was washed with toluene (3 × 30 mL). The product was then purified by flash chromatography using a silica column (DCM/ethylacetate 9:1) to obtain the white solid 3-Maleimidopropionic acid.
